What to Expect from The Well Dressed Life in 2020

As we gear up for the holidays and the New Year, I want to use today’s post to let you know what you can expect from The Well Dressed Life in 2020.

I’ve been thinking a lot over the last few months. I’ve spent days studying our analytics, and privately talking to a select group of readers in an effort to figure out how to continue to grow our site.

Now that I’m in my 40s, I know firsthand how challenging it is to get dressed every day, and look and more importantly feel, chic and modern.

Balancing that with our busy lives, realistic budgets, and a desire to stay youthful, is overwhelming – and I say this as someone who has dressed thousands of women professionally for over ten years. 

So I’m excited to share some things to look out for as we head into the New Year. 

Looking to 2020 

What to Expect from The Well Dressed Life in 2020
I love this coat. See outfit details below.

First, our daily content will continue through the remainder of December, with the exception of Christmas Day. 

On Friday, December 20th I am announcing a brand new Wardrobe Challenge, designed to help make 2020 your most stylish decade ever. It will kick off on January 10th.

All of the challenges will be posted on the blog, but it will be helpful if you also follow along on Instagram and in our private Facebook group. 

A Style Resource for Women 

The most significant decision I made for 2020, is that I’m going back to my roots. I spent all of my career as either a retail buyer or stylist and eventually owned my own styling firm. My talent is in deciphering what someone needs, and matching their style with what is in stores.

Over the last few weeks, I’ve walked through every store imaginable, scoured all the popular websites, and I can tell you without a doubt, it’s more challenging to shop now than ever before.

There are so many bad options; it’s almost impossible to see the good ones. And I guess I shouldn’t be surprised, but I can’t believe that designers, brands, and retailers are still marketing to a much younger demographic.

No one is focused on the professional woman, who needs a skirt she can sit down in. Or a  busy mom who doesn’t want to look frumpy just because she needs to be practical. What if you just want to go out with some friends, or go on a date and would prefer a top not cut down to your belly button?

I don’t know about you, but I feel like now that I can buy what I want and need, there is so little out there for me.

Our Readers

As I focused on our audience I was delighted to learn about the vast age range of our readers are anywhere from 30 to 70 year old.  Which just tells me that classic, timeless style is just that – classic and timeless.

Some of us work full time in the home, some outside, some both, some are retired. What we do with our days is different, but our desire to look and feel great in what we are wearing is the same. 

Our Content

Going forward, most of our content is going to focus on providing inspiration and advice to help you get dressed for your daily lives. And we are going to organize the site so you can navigate it easier. 

I want you to come here first if you need a new pair of jeans, or a great pair of heels for work. Stay tuned in the coming weeks for the first beta test of that functionality. 

I want you to think of this site as your very own digital personal shopper. Except this is totally free, there is no membership fee, no subscription, no box service, just daily tips, tricks and insider knowledge.

Starting in January, I’m organizing the content each day of the month as if it were a page in a magazine.

We’ll kick off each month with an Editor (that’s me!) Note. I think it’s essential that you know who I am and my perspective. This post will help provide some context for the month, give updates on what’s happening with the site, and a little insight into who I am.

Outside of that, I’ll share more personal and behind the scenes glimpses on Instagram, along with content specifically for the platform.

Our private Facebook group will remain a space to come and share thoughts, insights, and questions with other like minded women. It’s an exceptional group of women, who are kind and supportive of each other. (This is an women only group, all readers are welcome, please be sure to answer all of the membership questions to get approval.) 

After that, each day will focus on how to articles, roundups, size inclusive recommendations, lots more real life photos, wardrobe challenges, workwear inspiration, what to buy where, and more. Each post will all continue to be conversational in tone, but I’m pulling back on a lot of the other content. 

Of course, please continue to use the comment section – it’s where I get many of my ideas for articles. 

How the Business Makes Money

Which leads to the next question I always get: where does my revenue come from?

First, it’s important to know that I do not post sponsored content. (Sponsored content is when a brand pays you to promote its product.) It’s a business decision I make on a case by case basis. So far, I’ve declined every opportunity presented to me because it wasn’t on brand. 

That’s not to say I’ll never do it, but it would have to be a brand I’ve long promoted on my own and makes sense to our audience. It’s taken me too long to build a loyal following, I’m going to compromise that for a quick pay day. 

I also do not take goods or services in exchange for a review. Everything I wear I purchase myself, and if I recommend something it’s based on my personal experience and/or from my years as a stylist and personal shopper.

I currently make money two ways: online ads and affiliate links.

This year I was accepted into an ad group called Mediavine. Mediavine sells space on my site to advertisers and I’m compensated on impressions and clicks. It’s been a game changer for me in terms of becoming profitable without having to compromise my content.

I also make a small amount of money if you click and buy from one of our links.

That’s it. 

I’m playing the long game with this, so any time you visit, shop or refer us to a friend, you’re helping us grow one person at a time. 


The best use of my talents is in helping you navigate the overwhelming world of retail, which does nothing to make life easy for grown women.

I want this to be a helpful resource for you, the first place you go if you need something.

In 2019, I tripled our readership, which was an enormous accomplishment since I had a newborn and I still don’t feel like I know what I’m doing. 

This year, my goal is to tighten our message and continue to expand our reach. I also want to hit 10,000 followers on Instagram so that I can unlock their business features. (Follow along here, I promise I’m not annoying.)

Stay tuned for more updates and new features in the coming weeks. 

Real Life Outfit

What to Expect from The Well Dressed Life in 2020

Shop the Look: Coat $70 / Pants $89 / Top $18 / Pump $120

The scariest thing I did this year was put myself on these pages. I spent years avoiding it, but finally took the plunge.

I had Vivian last December (she turns one next weekend!) and I was not feeling great about my body and was obviously exhausted. But I think it’s important to see what things look like on a normal woman, with a regular life, who is not a model, and riddled with her own insecurities. 

Today I’m sharing this pulled together look that’s super easy to create. The coat is the key piece here. It’s more like a topper, or a long blazer than a coat for warmth. If I were going into an office, I would leave it on during the day but keep a long sleeve option underneath if it gets too warm. 

The coat is a new purchase, everything else I had in my closet. 

Shop the Look: Coat $70 / Pants $89 / Top $18 / Pump $120

I really consider our readership with every new decision I make and I pour so much of myself into every post I put out. I’m feeling pretty good about everything I plan on accomplishing in this new decade and I’m grateful you are part of our growing community. 


What to Expect from The Well Dressed Life in 2020

24 thoughts on “What to Expect from The Well Dressed Life in 2020”

  1. Hi, You look amazing and I love the outfit that you have on, I plan to emulate it!! I totally agree with your comments, I am an avid shopper and there is nothing that is chic, up to date and comfortable to wear. I was advised by a very chic and fashionable Aunt that “darling you become invisible after you are 40, and the trick to not allow it” I must say that seems to be the truth! I look forward to your posts, and be nice to your self!!

  2. I just want to say a big thank you to you. You are my go to for styling, business and business casual. I am looking forward to 2020 and styles that you have in mind.

  3. Thank you for sharing your look ahead into 2020. You say you’ve made a “significant decision” to go back to your roots – and to be focusing on content that helps women get dressed for the day. What feels most significant about this decision? What tough choice did you have to make? Will you stop doing something major? Just curious what you’re stopping or getting away from – maybe I missed that. I admire your integrity – not bowing to sponsors – playing the long game. In the modern day ad-littered, sponsored-everything blogosphere, your approach is as refreshing and rare as a friend who puts their phone down to look you in the eye and have a real conversation. I am encouraged by your honesty and your willingness to put yourself out there – BTW, you look incredible!!

  4. I love you and your blog, Megan. Thank you for what you put out there and who you are. And a HUGE CONGRATS on Vivian’s upcoming first birthday!!!

  5. YES!! I love your blog and really look forward to your style advice and savvy, as I feel like you are one of the few “real” bloggers who shares my struggle with finding something appropriate at the stores. I love all of your content, but really look forward to the fashion/style stuff as I am getting so fed up with shopping. Your practical and thoughtful advice has saved me many times. Happy holidays to you and your family & looking forward to a new year!

  6. Thanks for sharing your future plans a Megan. Your email articles are the only ones I actually save as they come through because they are so helpful! As I’ve gotten older (just retired) I’ve started buying key pieces of high quality (ie Stuart Weitzman boots) to save my feet, and looking for bargains in other clothes or shopping sales in department stores. Your advice has been helpful in seeking out the good pieces.

  7. Megan—I really, really love EVERYTHING about your plan moving forward! I’m so excited to have a wardrobe challenge to start the new year! And can I also say how much I appreciate that you purchase everything yourself and aren’t just pushing a certain product or piece of clothing to make a buck?! I feel like that makes you and your site SO MUCH more authentic, and I love that so much! And finally—I really like that you’ve added yourself to your page this year. It makes such a difference to me to see clothing items on a real body! I hope and pray that 2020 is your most successful year yet!! Love and blessings, Karen

  8. I really appreciate your style tips and recommendations! I’m more of a classic style person but don’t want to spend a huge amount of money and your suggestions are great. Thanks for everything you share!

  9. I love this focus; as a 41 year old I am nodding my head in complete agreement as I share the frustration of searching for appropriate, stylish, classic pieces in stores!! There are so many trends that do nothing to flatter the majority of female bodies 🙄 I have shared your blog with friends as I find it a breath of fresh air. Thank you! Best wishes for a happy Christmas and New Year 🎄

  10. Megan I am so grateful for your content and your honest approach. I recently purchased the wrap dress you featured from Amazon (I was luckily able to purchase it from the Canadian site) and I love it! When you review something I feel confident that it is a quality item and I really like that you are willing to post photos of yourself as opposed to viewing clothing on ultra-thin models with no curves that we see on store websites. I have nothing against those young girls but it is not realistic for me to expect clothes to look the same on me at 5′ tall and busty. You really understand the challenges most of your followers face! The clothing you feature translate well in the real world and I look forward to your content in 2020!

  11. This is all wonderful news, Megan! I wish you nothing but luck as you move forward with all of your plans.
    I have often remarked that because I am over 20 and don’t work at the beach there are very few retail options for me!
    I sew most of my own clothing for this reason – however, I have found your website so very helpful when looking for suitable undergarments, shoes and bags, and most of all styling ideas.
    I hope that you and your family enjoy a wonderful Christmas and I look forward with anticipation to following you in 2020.

  12. This all sounds great, Megan! I’ll just echo everything that has already been said. Thank you so much. Holiday blessings to you and your family!

  13. Please please look at leggings more critically. They are not flattering. Very few people should wear them. They do NOT enhance your appearance.

    I enjoy your blog tho.

  14. Hi Megan,
    I am one of you UK followers, and I love what you post,say and do and I try to find similar products in the UK inspired by your content. Just so you know the shopping experience in the UK is the same situation….there is a bewildering array of expensive bad choices for the 40 plus lady!
    Keep up the brilliant work that you do and I look forward to our Well Dressed life journey in 2020.
    Oh and by the way you look fab!

  15. As I live in New Zealand I don’t have the option of just popping off to the shops to buy a anything I see on your blog that I love. I am interested in which stores ship Internationally. So many don’t. Can you write about that sometime and possibly give some insight into why?

    Thank you and Merry Christmas.

  16. I LOVE your new “What to buy where” posts! So incredibly helpful 🙂 Looking forward to seeing what the new year brings!

  17. I just want to let you know how much I enjoy your blog and look forward to the next challenge in 2020. I am one of your older readers, 68 and retired. My 28 year old daughter also reads your blog. Both of us love it!

  18. I’d love if you would share your lip color as part of a look, especially if the lip is a bold pop like this one. Thank you for more photos of you this year. I know it was a stretch outside of your comfort zone but really did make reading your posts nice. I look forward to your blog updates in my inbox and look forward to the change in your platform this year. I wish you a wonderful year and much success and happiness.


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